Benzyl Alcohol → HCID 20448817, compound

HRID 358367Notes

Reaction equation

HRID 358367 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][C:11](=[O:13])[C:10]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:9]1.ClC(OCC(C)C)=O.C(N(CC)CC)C.[CH2:38](O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][C:11](=[O:13])[C:10]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:21])=[CH:9]1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 20448804HCID 20448804, compound

Product 1

HCID 20448817HCID 20448817, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

2.09 g (6.1 mmoles) of 4(RS)-tetrahydropyranyloxy-2-(5-carboxypentylthio)-2-cyclopentenone was dissolved in 20 ml of dichloromethane, and to this solution were added 5 ml of a dichloromethane solution of 956 mg (7 mmoles) of isobutyl chloroformate and 5 ml of a dichloromethane solution of 808 mg (8 mmoles) of triethylamine. The mixture was stirred at -78° C. for 30 minutes. Then, 5 ml of a dichloromethane solution of 864 mg (8 mmoles) of benzyl alcohol was added, and the reaction was carried out for 18 hours while gradually raising the temperature to room temperature. After the reaction, the reaction mixture was extracted with ethyl acetate. The extract was washed with an aqueous solution of hydrogen chloride and an aqueous solution of sodium bicarbonate, then dried, and concentrated. The resulting crude product was chromatographed on a silica gel column using hexane/ethyl acetate (3.5/1) as an eluent to give 1.30 g (3.11 mmoles; yield 51%) of 4(RS)-tetrahydropyranyloxy-2-(5-benzyloxycarbonylpentyl-thio)-2-cyclopentenone.

Workup

  1. waitthe reaction was carried out for 18 hours
  2. temperaturewhile gradually raising the temperature to room temperature
  3. customAfter the reaction
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of hydrogen chloride
  6. dry with materialan aqueous solution of sodium bicarbonate, then dried
  7. concentrationconcentrated
  8. customThe resulting crude product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-cd6c4a1d83cb4e199d2c817d1745a00f
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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